


Why Does It Have To Be (Wrong Or Right)

by outoftheashes



Category: Supernatural
Genre: Alternate Universe, Angst and Fluff and Smut, Angst with a Happy Ending, Bottom Dean, Bottom Jimmy, Butt Plugs, Castiel and Jimmy Novak Are Twins, Cock Piercing, DCJ Big Bang, DCJ Big Bang 2017, Dean Winchester/Sam Winchester UST, Dom Castiel, Dom/sub, Dom/sub Undertones, First Time, First Time Blow Jobs, First Time for Everything Fest, Group Sex, Ink, M/M, Multi, Orgasm Delay/Denial, Pain, Piercings, Polyamory, Sibling Incest, Sub Dean, Tattoo Artist Castiel, Teacher Sam, Teacher Sam Winchester, Threesome - M/M/M, Top Benny, Top Castiel, Top Castiel/Bottom Dean Winchester, Top Sam, Twincest, Waiter Dean
Language: English
Status: Completed
Published: 2017-05-17
Updated: 2017-05-17
Packaged: 2018-11-01 19:41:09
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,109
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10928697
Author URL: https://archiveofourown.org/users/outoftheashes/pseuds/outoftheashes
Summary: When Sam and Dean enter a tattoo parlor on Sam’s birthday Dean’s drawn to Castiel, the grumpy owner, and his twin brother Jimmy. Right away he learns that Cas and Jimmy are in an incestuous relationship and the adjustment period is surprisingly easy.After Dean, Cas, and Jimmy get together Jimmy drops a bombshell - he wants to bring a couple of friends into their bed for a night. The problem? None of them know anyone they trust outside of Benny and Sam. And Jimmy really, really, really wants Sam to fuck him.





	Why Does It Have To Be (Wrong Or Right)

**Author's Note:**

> This fic was written for the DCJ Big Bang on Tumblr. Thanks so much to all the lovely mods for being so chill and making this experience as laid back as possible. Thank you to my friend and artist Maya for your awesome headers, edits, etc. Thank you to countless other friends who were cheerleaders throughout this whole damn thing. Without you, I would have dropped out a long time ago.
> 
> This is my first time writing Dean/Cas/Jimmy, so please be gentle. Holy crap. Jimmy was such a blast! Just a heads up: this is, without a doubt, "fanon" Jimmy. His personality isn't much like how it is on the show. Next time I'll try a more canon approach, I think. 
> 
> Tried to write this without Sam. Didn't work. I'd say sorry but it'd kinda be a lie. 
> 
> Enjoy!

__

 

_Dude, get your ass out here! No bailing on me._

It's Sammy's birthday and Dean wants him to get laid. His little brother is more than a little high-strung and a nice fuck sure as hell wouldn't do him any harm.

He's not gonna take no for an answer, not this time. His brother is too young to stay cooped up all alone. That's why Dean's chilling under some shade in his Impala, waiting for Sam to stop hiding.

His phone buzzes and Dean checks for a new text.

_Any five-year-old in my class has more patience than you._

Dean smiles.

_Bitch._

A few seconds later his cell phone vibrates again.

_I'm coming, jerk._

Dean sighs in relief when his brother walks out of the school. The kid is wearing jeans and a white button-down shirt, his hair dancing around his head and getting tangled from the wind.

“You look like a nerd!” Dean calls out the window when Sam's close enough to hear him.

Sam rolls his eyes and jogs the rest of the way, quickly hopping into the passenger seat. “Remind me again why I'm wasting my birthday with you?”

“Because I'm awesome.”

“Uh huh.”

“S’true. So, how are things?” Dean asks like he doesn't already know as he pulls out of the parking lot.

“Ruby’s still acting out in class, but I’ve got it under control. Ben is still behind but isn’t struggling with high frequency words anymore. Most of my kids can write their first and last name. Math has been a challenge, but we’re getting there.”

Dean snorts. “You sound like a proud papa.”

“I kinda am. I _do_ see them nearly every day, you know.”  

Dean nods and drops it. Truth is, he wants more than that for his brother. He always thought he'd be an uncle by now, but Sammy is as single as ever. He can't say what's on his mind, though. Not if he wants this day to end on a high note.  

“Know where I wanna take you.”

Sam groans. “Dean, no. I hate going out.”

Dean flashes his brother a grin. “That's just too damn bad, Sammy boy.”

“Okay, but it can't be a late night,” Sam says, using his I’m-very-serious-about this-Dean voice.

“Hell yeah, it can! We’re gonna stop by a tattoo shop and hit up a bar -”

“You're fucking insane,” Sam interrupts him, shaking his head.

Dean gives a fake, childish pout. “Ah, c’mon. I'm not that bad.”

He can _feel_ Sam glaring at him.

“What are your expectations for the night, exactly?”

“Get you a little drunk. Maybe see you get inked. Hopefully, you'll take a girl home.”  

“God.” Out of the corner of his eye, he sees Sam run a hand over his face. “You're something else, you know that?”

“I do know that. I also know you need to learn how to chill the fuck out. Don't be such a tight ass.”

“I hate you so much right now.”

“Yeah, but you'll thank me later.”

 

* * *

 

 

Novak Brothers Tattoo and Piercing doesn't look quite how Dean pictured it would. White walls, wide windows, a hardwood floor and deep purple couches with fluffy pillows in the waiting area… it's not _bad_ , just not what he expected from the ‘best in town.’

Then again, when it comes down to it, looks don't really matter -- just the talent, right? Word of mouth says the Novak brothers will do you right, so he's willing to take the chance.

When Dean catches a man at the front desk staring at them his chest feels heavy and he can barely breathe. If the dark, wild sex hair wasn't enough, his piercing gaze sure is.

_Oh, fuck._

“Welcome to Novak Brothers Tattoo and Piercing. What can I do for you?”

Sam clears his throat and takes a few steps toward the man, moving close enough so he's almost pressed against the counter.

“My brother wants me to get a tattoo.”

“Do _you_ want one?” the man asks, quirking a brow. “People who come here on a dare or while intoxicated regret it later.”

A few beats go by before Sam says, “yes.”

Dean's too flustered to chime in, opting for staring dumbly at this attractive but grumpy man. If the neck tattoo peeking through his long-sleeved shirt is any indication, he’s covered in ink.

“What's your name?”

It takes Dean a few seconds to answer. “Dean. And that's my baby brother Sammy. And, uh. You are?”

“Hello, Dean. I'm Castiel Novak, owner of the shop.” Cas’s eyes turn back to Sam. “Do you know what you want?”

“Um. I'm really into protection symbols and Latin…”

Cas raises a brow again then nods, pulling out a binder and handing it over. “Here’s a portfolio of the work we do here. Why don’t you take a seat, look through it and see if the style is to your liking?"

“All right.” Sam stumbles off, a little wide-eyed and Dean wants to follow him except -

Cas is staring.

Dean gulps. “H-hey.”

“Are you here for moral support or are you getting work done?”

All business then.

“I was actually, um,” Dean pauses, rubbing the back of his neck. “Considering a piercing.”

“Where?”

“Uh. My dick.” 

“What kind of piercing?”

“Prince Albert.”

“Would you like a topical anesthetic?”

Dean waves off that idea. “No way."

“Are you aware of the healing time? That you can't have sex for four to six weeks afterward?”

Dean hesitates at that, because okay, that doesn't sound like fun. He loves sex. Is fucking ravenous for it. Going without sounds like a form of torture he's not sure he can handle.

“Yeah. I can handle it.”

“Jimmy will discuss in greater depth what you need to do and what to avoid. Would you like to see him now?”

“No. I, uh. I'm gonna wait for Sammy.”

It wasn't long, thankfully. Sam came back, a hesitant smile on his face. “I want the Eye of Horus.”

“You're such a geek,” Dean says, hip checking his brother.

 

* * *

 

 

Jimmy, Cas’s twin brother, has the best smile. It's wide and holds nothing back. He's fucking _happy_ , genuinely pleased to see him and Sam and it's refreshing as hell.

“I'll pierce you,” Jimmy says. “Unless you'd rather Cas do it?”

Unlike Castiel who is damn near impossible to read, Jimmy makes his interest in Dean crystal clear, licking his lips and eye-fucking him in a completely unapologetic way.

“You're fine,” Dean replies, eye-fucking him right back.

“You guys are so obvious it's painful,” Sam says with a snort.

Dean elbows him. “Shuddap, Sammy boy. Don't be such a prude.”

“Really, Dean? Wanna try that again? If you were anybody else I wouldn't care, but you're my _brother_. Of course, I'd rather not see this.”

Dean's about to make a snarky comment when Jimmy interrupts them.

“I've sterilized the area. Go ahead and take a seat,” he says, looking amused.

Dean obeys, sitting on the chair, placing his forearms on the arm rest.

“Well, let's get on with it,” Jimmy says with a smirk.

“You just wanna see my dick,” Dean accuses, giving Jimmy a huge grin as he takes out his cock.

“Hell yeah, I do. Do you blame me?”

Thankfully Sam has made himself scarce. He's not sure if his brother is out in the front of the tattoo shop or in another booth, but he honestly doesn't care.

He's not sure when Jimmy put gloves on or if he's had them on the whole time, but he notices them now.

_Fuck. It's really happening._

Jimmy carefully cleans Dean's cock, paying special attention to the tip of it.

“Ah, f-fuck.”

He's sure it's supposed to feel detached and professional, but Dean just finds it hot.

“Not getting excited already, are you?” Jimmy teases.

“Hey, fuck you, man. _You_ try having a guy as hot as you do this.”

“How do you know I haven't? Have you _seen_ my brother?”

Dean blinks, brain short circuiting. “Uh…”

Jimmy looks far too delighted for Dean's liking as he takes a marker with a very fine point and marks his cock. Afterward, he holds up a mirror so Dean can easily see the entrance and exit points.

“This where you want it?”

"Yeah, looks good.” 

“I think so, too.” Jimmy nods and pulls on a new pair of gloves.

It all happens quickly after that. The worst part is when his urethra gets pierced, but honestly, it's still pretty hot. He lets out a sharp breath upon feeling the needle and Jimmy smirks in this way that makes Dean wanna fuck his face.

Once the jewelry is inserted there's a dull, pleasurable ache in his cock. He wants to come. _Needs_ it. Nobody fucking warned him about that. Does that mean he's a freak?

“Jesus Christ,” Dean finally grits out.

“Thought you were a big boy and didn't need an anesthetic,” Jimmy teases, unaware of Dean's issues.

Or maybe the asshole wants him to say it out loud. Fucking hell.

“I didn't. It's… I like it,” he pants. “It feels awesome.”

“Huh. Well, please remember you can't have sex, especially oral, for at least four weeks.”

Dean groans. “Yeah, your brother already told me that. Think I made a big mistake.”

“It's infection we’re concerned about,” Jimmy says, for once looking serious. “The pain doesn't last long, but you still need to hold off. If you don't it'll slow the healing process, so be a good boy, okay?”

“Yes, sir,” Dean says with a smirk.

Jimmy gives him a little speech about piercing aftercare and Dean does his best to pay attention, but honestly, he's _way_ too distracted by Jimmy's pretty mouth.

“You're not listening,” Jimmy says.

“Nope!”

“This is important, you know.”

“My nerd of a brother is gonna ask enough questions for the two of us. I think I'll be fine.”

Jimmy rolls his eyes. “If you come back with an infection I won't feel bad for you.”

 

* * *

 

When Dean heads over to Cas’s booth to see how Sam's doing he's faced with quite a sight: his baby brother gasping, hips rolling, face flushed and mouth parted as Cas inks his forearm.  

“Oh shit, oh f-fuck. _God_."

“Let go, Sam,” Cas says, voice gravelly and demanding.

He looks _wrecked_. Like he's getting fucked by Cas.

“What the -”

Sam interrupts him with a groan, jeans darkening and _Jesus fucking Christ_ he’s just standing here while Sam’s _coming_ in his pants.  

Apparently, both of them have a pain kink.

That's all kinds of fucked up in ways he can't even begin to process right now, but he can't run because Sam and Cas are staring at him.

“M’sorry,” Sam gasps and Dean's not sure who he's talking to.  

“Sammy, you're a smart boy. I bet you've done tons of geeky research and know this shit can happen. Chill out, you're all good you kinky bitch. Right, Cas?”

“I've been trying to tell him as much for the past five minutes.” Cas shakes his head. “He wouldn't listen.”

“That's Sammy for you.”

“Jerk.” Sam glares at him.

Dean puffs his chest out proudly, trying to hide how he is internally screaming. “Nuh uh. I'm adorable and awesome.”  

Sam rolls his eyes.

“Are you done with your annoying banter now?”

Sam flushes. “Yeah.”

“Good,” Cas says with a satisfied look. He pulls on new gloves and gets back to work, making Sam moan in ways that are disturbing as hell and he kinda wonders if -

“Nope, nope, nope! I'm out,” Dean says and runs out of the booth.

 

* * *

 

 

Cas and Jimmy close up shop and Dean can't stop looking at them. The way Jimmy laughs and slides his hand up Cas’s arm is… interesting.

“Hey, Sammy,” Dean says, clapping him on the back. “Ready to hit up a bar? We could stop by your place first and -”

“Nah, I think I'm just gonna take a cab home."

Dean frowns. “No way! It's your birthday, dude. That's not happening.”

“I know you wanna fuck around,” Sam says bluntly. “I'll just get in your way.”

“It's your birthday. I wanna hang out with _you_ , Sammy. Yeah, the twins are hot, but I can just grab their number, no big deal.”  

“Too bad,” Sam says, stepping away from him. “I really just need to leave. Okay? I need some space.”

“At least let me take you home. Do you really want people seeing you when you've got come in your underwear? C’mon, man. Don't be like this.”

Sam gives him a dirty look. “Goodbye, Dean.”

Then he stalks off.

_Dammit._

How could he have screwed the night up already? It wasn't even midnight!

“Hey, Dean. Are you all right?” Jimmy asks as he sidles up to him. “Why'd Sam leave? Thought it was his birthday.”

Dean runs a hand over his face. “I don't really wanna talk about it if that's okay with you.”

Jimmy nods. “I understand. Um, I know this is weird, but would you like to hang out?”

Dean bites his lip and shuffles closer to Jimmy. “I know just the place.”

Twenty minutes later they pick a booth at Denny's - Dean takes one side and the twins are on the other. Jimmy drapes an arm over Cas’s shoulders and Cas tries to shrug him off but Jimmy keeps touching him until Cas sighs, giving into his brother. Dean orders a bacon cheeseburger, Cas gets a sampler platter and Jimmy chooses the bacon lover’s blt.  

“Shit. You might like bacon more than I do,” Dean says with a laugh.

“He’d live off of it if I let him,” Cas says, shaking his head.

“That's because bacon is amazing,” Jimmy says, tone serious.

Cas shrugs. “I prefer steak. A nice filet mignon. Maybe a prime rib. Bacon is fine. I also feel as though this conversation is useless. How about we talk about the obvious?”

“Which is?”

“You want Jimmy.”

Dean chokes on his water then licks his lips. “Yeah, maybe I do. So what?”

“What if I want you, too?”

“Uh.” Dean rubs at the back of his neck. “That could get complicated, but I'm sure we could work something out.”

“Before this goes any further there's something you should know.”

“Oh no,” Dean teases. “That's not very reassuring. You're not serial killers are you?”

Cas snorts. “Hardly.”

Jimmy glances around Denny's to make sure no one is eavesdropping and lowers his voice. “We fuck.”

“Come again?” Dean asks because he could _not_ have heard that right.

“My brother likes to hold me down and fuck me until I scream,” Jimmy says with a heated look.

Cas reaches out and steals some of Dean’s fries, eyes darker than Jimmy’s. “Can you handle that, Dean? Or are we wasting our time?”

Dean's mouth is dry and his cock _really_ wants to get hard.

“Fuck yeah. I can handle it. That's _hot_.”

Dean doesn't tell people - obviously - but he's got a bit of an incest kink. And twins are his favorite.  

“Really?” Cas looks surprised.

“Dude! Of course, it is. Besides, you guys don't seem to know what personal space is. Kinda obvious _something_ was going on.”

“That's your fault,” Cas grumbles, turning his head to stare at Jimmy. “My brother is more physical than I care for when we're out in public. Thinks it's exciting.”

“That's because it _is_ ,” Jimmy says, almost singing the words.

“Well, whatever. I don't care. Do it in front of me all you want.”

“It's a shame you got your cock pierced,” Jimmy says, licking his lips. “Now I can't suck it.”

Dean whines. “That's… really not fair.”

The glint in Jimmy’s eyes is impossible to ignore. “Would you like to watch me suck Cas’s dick?”

“Dude. Is that even a question?”

 

* * *

 

 

“How long is it gonna feel like this?” Dean complains once he’s inside the twins small but cozy apartment. “The pain… it won’t go away.”

“The heavy ache will disappear in around four hours,” Cas says, eyes dark. “Why?”

“I can’t get soft.”

Jimmy groans. “Fuck.”

“You’ll have to suffer a little longer. I’m sorry.”

Dean narrows his eyes. “You don’t sound very sorry.”

Cas shrugs. “I suppose I’m not.”

Every time he takes a step his dick drags against the inside of his boxers and he has to bite back a whine. “This fuckin’ PA was the worst idea ever.”

“You’re such a baby,” Jimmy says with a chuckle.

“Sit,” Cas orders after dragging a chair into their bedroom.

“Seriously?” Dean frowns at it but obliges.

Cas ignores him, cupping his brothers face. “On your knees.”

Jimmy doesn’t question it, obeying faster than Dean and hits the floor in seconds. It’s hard to see from this angle but Dean’s pretty damn sure Jimmy licks his lips as he stares up at Cas. “Please.”

“Do it.”

Jimmy whines, removing Cas’s dick from his pants and Dean grips the arms of his chair, leaning forward to try and get a better look.

“Don’t move,” Cas growls and Dean jerks a little. He hadn’t realized Cas was paying any attention to him and his reactions.

“What’ll happen if I disobey?” Dean asks, Adam's apple bobbing and feeling far more turned on than he’d expected after his recent dick piercing.

“The sweetest torture you’ve ever experienced,” Cas says. Judging by his voice alone Cas sounds painfully in control - but his eyes tell a different story. There’s barely contained desire burning in his gaze.

Jimmy swallows Cas down and Cas growls, fisting a hand in his brother's hair as he stares at Dean.

“I don’t see how that’s any different than what I’m experiencing right now,” Dean can’t help but point out.

“More of the same,” Cas suggests a little breathlessly.

“Come on,” Dean begs. “Need to know more than that.”

“When we finally get our hands on you maybe we’d draw it out.”

“You’re assuming there’s gonna be a round two. That was your first mistake. I’m not the kind of guy you take home to Mom and Dad. More of a love ‘em and leave ‘em kinda deal.”

“We’ll see.”

“Christ,” Dean whispers, cock thickening. He should _not_ be so fucking turned on by how cocky Cas is.

Cas _smiles_ and focuses his attention on Jimmy, who’s been obediently sucking his dick throughout their conversation. He thrusts into his brother's mouth gently and the look of fondness on his face takes Dean’s breath away.

“I’ve never seen a guy get so hungry over sucking cock,” Dean says, licking his lips.

“He gets much needier when my dick is in his ass,” Cas breathes.

The noises coming out of Jimmy are driving Dean insane. He moans as if _he_ were the one getting sucked off and holy _fuck,_ what Dean would give to do that for him.

Dean’s eyes keep darting between the two brothers, afraid of missing anything. Cas comes on a groan, head tilting back in pleasure, hands still buried in his brother's hair as Jimmy drinks him down. Dean yearns to capture the moment, to save a picture and remember but it’s too late to ask now - Cas is already composing himself.

“Can I take care of Jimmy?” Dean asks, squirming in his seat.

Cas raises a brow and for a terrible moment he’s afraid he’ll say no, but he shrugs. “Why not? If Jimmy wants -”

“I do!” Jimmy rasps as he pulls off of Cas’s now soft cock. “I definitely do.”

Despite having just come Cas looks _hungry_ as he stays near his brother. “Crawl,” he tells Dean.

“W-what?”

“If you want my brother so badly you can crawl over here and take him. Unless you have any objections?”

Considering the demands that have been made thus far he can’t say he’s surprised. Dean slips out of his chair and onto his hands and knees. “I don’t object.”

“Good boy.”

_Holy shit._

He likes that. He likes the sound of  _good boy_ on Cas's lips, especially when directed at  _him._

He takes his time making his way over to Jimmy, who’s still on the floor. Jimmy looks fucking _ruined_ and Dean wants a turn doing the teasing, dammit.

Jimmy falls onto his back, legs spreading so Dean can easily move between them. “God, aren’t you eager?” Dean purrs, yanking Jimmy’s pants open.

“No more eager than you.”

“I’m gonna enjoy this."

“So hurry up and _do it,”_ Cas growls low in his throat and Dean shivers before swallowing Jimmy down to the base of his cock in one go.

 

* * *

 

 

Normally there’s no real desire to reconnect. Dean’s happy on his own with only Sammy for company.

He can’t say it applies anymore. Every time he gets off work Cas and Jimmy pop into his mind and at first, he resists - but after two weeks of obsessing over the twins he gives in and goes to their shop.

Jimmy’s face lights up when he enters. “Hey, what are you doing here?”

“Ah.” Dean’s eyes wander around the room, unable to keep watching Jimmy. “I was wondering if I could stop by from time to time?”

Jimmy put his chin in his hand, resting against the counter. “Hmm. Well, I can’t speak for my brother, but I’d love to see you more regularly.”

“Awesome.”

 

* * *

 

 

Cas holds Dean’s dick near Jimmy’s hole and Dean almost cries due to the sheer cruelness of it.

“Oops, no, can’t do that yet,” Cas purrs, letting Dean’s dick go and giving it a playful pat.

“I wanna fuck one of you, dammit!”

“Patience is a virtue.”

“You’re loving this way too much. It's been  _three_ weeks since I've gotten the PA. That's long enough!"

Cas bends down, mouth mere inches from Dean’s cock. He can feel his hot breath on his skin. “No." 

“You’re fucking evil, dude.”

Cas laughs before nipping at the inside of Dean’s thigh.

“I believe Jimmy holds the title of ‘evil twin.”

“You have no idea how frustrating this is. I don’t think I’m gonna survive the night.”

Cas lubes up his fingers and presses one inside of Dean, making him whine when it nudges against his prostate. He’s barely been touched but he’s been fucked with for too many weeks without being satisfied. “But won’t it be the sweetest destruction?”

Dean can’t reply because he’s too busy marking Jimmy’s body with come.

 

* * *

 

 

Dean’s never been good with words and there’s no good way to say it anyway. So he doesn’t bother trying.

“Look, Sammy… I didn’t just invite you over for dinner.”

“I knew it,” Sam mutters. “You were acting really fucking weird on the phone. What’s up?”

“I’m dating the twins,” he says, then coughs awkwardly.

Sam blinks, shifting in the ugly wooden chair at the table. Dean’s been bugging Cas about getting another one because the thing looks about ready to bust apart, but Cas refuses to buy new furniture. Will only go for used stuff and Dean’s yet to find anything on Craigslist worth the effort to try and snag. Maybe he can talk Jimmy into going to a few yard sales with him -

Fuck. This is what Dean’s come to. He fucking wants to _decorate_ and leave his mark on the apartment he isn’t even technically living in.

He’s so screwed.

“Wait, what? Both of them?” Sam asks. "Haven't you only known them a couple months?" 

“Uh, yeah. Both of them. And it's been six months. Honestly, it's probably beyond dating at this point."

Sam drops his fork. “It’s not weird for you guys at all? I mean, how do you deal with the whole brother thing?”

“It’s not weird,” Dean says, smiling despite his nerves. “And, uh… we deal just fine."

Sammy takes a deep, cleansing breath and runs a hand through his hair. He looks like he wants to ask something but seems to think better of it. “You know what? I don’t wanna know. Congrats.”

Dean blinks. His chest feels tight and heavy. “That’s it? That’s all you have to say?”

“What do you want me to say? No? That it’s a mistake? Do you want me to tell you how sick it is and that you need help?” Sam asks, raising his eyebrows and spreading out his arms. “Come on, man.”

“What? No, of course not. You just… you’re such a chatty Cathy I was expecting more questions, you know?”

Truth is, a part of him was hoping that if Sam didn’t cut him out of his life that he’d be _excited._

“Well, I don’t know what to tell you, man. I’ve got nothing else.”

The smoke alarm goes off and Dean jumps.

“Ah! Fuck! The cookies!” Dean yells and sprints for the oven, Jimmy close behind him. “They’ve been in too long!”

“Dean.” Jimmy rests a gentle hand on Dean’s back. “Breathe. It’s going to be fine.”

“Well at least one of us is sure about that,” Dean says, pulling out the blackened chocolate chip cookies. He pouts. “No way am I feeding these to Sam.”

“You don’t have to. I’ll eat them,” Jimmy says, kissing Dean’s cheek. “You made a lovely dinner. It’s more than enough. Besides, doesn’t he have a fetish for salad? He’d probably decline the cookies anyway.”

“Still,” Dean grumbles, but he turns to kiss Jimmy full on the mouth.

Maybe it’s unfair, but he can feel disappointment bubbling inside of him, threatening to spill over and it’s _not_ because he screwed up dessert.

 

* * *

 

 

Sam cuts dinner short, spouting some bullshit about needing to go to bed early so he’s well rested for the field trip in the morning. And hey, it’s probably for the best, but it doesn’t stop Dean from moping around after Sam is gone.

“I don’t want to create any drama where there is none but…” Cas trails off, which immediately grabs Dean’s attention.

Dean raises a brow. “What?”

“You don’t think that Sam was acting a little odd?” Jimmy asks, grimacing as he takes a bite of cookie.

Dean rolls his eyes and throws the rest of them in the garbage. “Not any more than usual, I guess.”

“That’s the thing. He’s done this before - cutting time with you short when he has nothing else planned.”

“What are you saying?”

Cas nods at his brother. “The timing is awfully suspicious.”

Dean frowns. “In what way?”

“Nevermind.” Jimmy shakes his head. “I shouldn’t have said anything."

_That’s for fucking sure._

Now it’s all he can see and he has no damn clue what it means.

 

* * *

 

 

Most days Dean gets to be the middle spoon and today is one of them.

Christ, he's a lucky sonofabitch.

He stretches in their king size bed, letting out a groan of satisfaction. Dean watches his lovers,  seeing if either of them is awake - they’re not. Time to change that.

“Morning, sunshine,” Dean says, shaking Cas awake.

“Hello, Dean,” Cas says, raising a brow. Dominance radiates off of him.

_Oh, fuck yes._

“What's wrong, baby? Little early for you to be pissed already, ain't it?”

“Do you _want_ a spanking, Dean?”

Dean shivers, licking his lips. “Maybe.”

“Stop being insufferable.”

Jimmy throws an arm over Dean in his sleep, nuzzling closer. It’s distracting as hell.

Outside the bedroom, he'd rather not, but in the lazy morning hours, he cuddles his boyfriends. Okay, mostly Jimmy. Jimmy is easily the most touch-starved out of the three of them. So he runs his fingers through his hair and caresses his pinkened cheeks that make him look almost angelic in sleep which is hilarious considering he’s anything but and is often called the ‘evil twin.’  

“Ah, c’mon! You had to wake up sometime, Cas. Couldn’t just let you sleep all day.”

Cas’s eyes soften as he watches Jimmy. It's a special look that's reserved only for him. Whether it's because they're twins, Dean's hard to love or both Dean's not sure, but it doesn't matter much. What matters is Cas trusts Dean enough to let him see this gentle version of himself. It’s a testament to the trust that has grown between them.

“You're walking a fine line, Dean.”

“That so?”

“Yes.” Cas’s gaze flicks up to Dean's face, those piercing blue eyes taking his breath away. “Unless you want to be put in timeout…”

Cas’s voice trails off, allowing Dean to fill in the blanks.

There are times Dean really fucking loves being punished. Today he's not feeling it quite as much.

“No, Cas.”

“Good.”

And with that Cas pulls Dean on top of him and kisses him breathless. He can hear Jimmy whining in his sleep and can't help but smile against Cas’s mouth.

Today's gonna be fucking awesome. He just knows it.

 

* * *

 

 

A few minutes later Cas has _finally_ stopped teasing Dean.

For the most part.

He pulls his fingers out of Dean's ass far too slow for Dean's liking but is thankfully quick to flip Dean over onto his hands and knees with ease and slide into his lubed ass in one long delicious thrust.

Dean whines, fucking back onto Cas’ cock, impatient for more.

Cas spanks his ass once. “You know the rules, Dean. Use your words.”

“F-fuck…” Dean still has a hard time asking for what he wants, but it's definitely getting better. “Fuck me rough. Want it to hurt. Please.”

“There. Was that so difficult?” Cas rasps, gripping Dean’s hips and fucking into him hard enough it knocks the breath out of him.

When Dean doesn't immediately answer he gets another swat on the butt, making his cock jerk happily.

“You know it is.”

“It’ll get better,” Jimmy promises, finally awake. There's a slight pout on his lips. Probably annoyed they hadn't woken him for the foreplay.

“Hey,” Dean gasps. “Get over here.”

Jimmy's eyes brighten and he rolls so he's snug against Dean. “What should I do with you?"

“Fuck his mouth,” Cas says. It's not really an order, but Jimmy obeys him anyway, getting on his knees and running his pretty cock over Dean's lips. The smell of precome is already thick in the air, making Dean's mouth water.

“Come on, suck me,” Jimmy breathes, looking excited as hell and it's got Dean's dick twitching again. God, he loves how eager Jimmy is. How unreserved.

“Take all of it. Choke on his dick,” Cas adds with a growl, snapping his hips.

Dean yelps and Jimmy takes the opportunity to rest his cock on Dean's tongue. Seconds later he sucks Jimmy down, caressing the underside of Jimmy's dick.

“Good boy,” Cas says, his thrusts turning wild.

Dean, of course, says nothing. He wants to see how fast he can make Jimmy come undone.

It doesn't take long.

“Please,” Jimmy whimpers.

He's not sure who Jimmy's asking and he doesn't really care.

“It’s all right, little brother. You can come.”

Jimmy's spunk floods his mouth seconds later and Dean swallows greedily, nursing every little bit of come out of Jimmy's cock before removing his mouth.

“Thank you, Dean.” Jimmy gently tugs on Dean's hair, making him moan softly.  “Will you come for us? Are you close?”

“Y-yeah -”

Cas slows down a little so he can snake a hand around Dean and fondle his cock and balls. “Give it up.”

Men or women expecting him to come on demand used to piss him off or give him performance anxiety - not so with Cas and Jimmy.

With a few more expert tugs and twists Dean's shouting out his release.

“Beautiful,” Jimmy says, tilting Dean's face up so he can look him in the eye.

Cas bites into Dean’s neck, _marking_ him and then Dean feels Cas’s cock throb in his ass as his come fills him up.

 

* * *

 

Once finished with aftercare and relaxing, they throw the comforter in the hamper and shower together before Dean cooks them all blueberry pancakes for breakfast.

Dean's shift at Denny's doesn't start for another hour, so he's looking forward to taking his time eating.

But then Cas is staring at him and Dean can't help but feel uneasy.  

“We need to talk,” Cas says once Dean joins them at the table.

Fuck.

“Uh-oh, what'd I do? Am I in trouble?” Dean tries to tease, but secretly he's freaking out. Hunger leaves him almost as soon as it arrived and he pushes his plate of food away.

“Of course not.” Jimmy reaches across the table to take Dean's hand, rubbing his fingers over Dean’s knuckles.

It helps. Barely.

“Well?”

Jimmy glances at Cas before continuing. “How do you feel about group sex, Dean?"

Dean blinks at Jimmy. “What?”

“My brother wants to bring a couple people into our bed for a night,” Cas says bluntly.

He can't say he's completely opposed to the idea.

“Jimmy, I didn't know you were _this_ into casual sex.”

“Oh, I am. Surprised I even have to say it.”

Dean snorts. “Okay… uh. Say I said yes. Are you wanting strangers? Grindr would probably -”

“No,” Cas cuts him off. “No strangers.”

“Uh. Okay. But that leaves friends. Wouldn't that be weird?”

“You used to have sex with Benny and that's not weird,” Jimmy points out. “What about him?”

Dean bites his lip. “He might be into it. Uh... So who else are you interested in?”

Cas and Jimmy share a look. Dean works hard to decode it and fails.

“Sam,” Cas finally says.

“Sam would be perfect,” Jimmy adds, a grin spreading on his face.

“The hell?!” Dean yelps, pushing back and away from the table. “No. I'm not fucking my baby brother!”

“You don't seem to have a problem fucking _us_ and _we’re_ brothers,” Cas says with a raised brow.

“It's different!”

Jimmy shakes his head. “It's really not.”

“I'm not fucking my brother,” Dean repeats slowly. He gets out of his chair and starts to pace.

“We're not asking you to,” Cas says.

“I’ll fuck him,” Jimmy explains. “If he'd be into it. Or Cas can.”

Dean stops pacing and stares at Jimmy hard. “I don't think my brother is into guys -”

“Oh, he is,” Jimmy says, voice soft and maybe a little breathy. “Trust me.”

Dean swallows hard. “I'm really not interested in seeing him naked -”

“You'll have myself and Benny to keep you busy,” Cas promises, standing up and moving towards Dean slowly. “Jimmy at some points, too. I don't think it'll be a problem.”  

Dean squints at Jimmy. “Do you _like_ Sammy?”

“What’s your definition of like, Dean?”

“Do you have feelings for him?” Dean clarifies.

_What if Jimmy doesn’t need me anymore?_

“No. I just think it'd be hot to get fucked by him once or twice.”

Cas is hovering near Dean, close enough he can smell his body wash, but he's made no move to touch him and it's driving him nuts. Jimmy seems to notice because he stands, quickly makes his way to Dean and pulls him into a biting kiss.

Dean melts, wrapping his arms around his boyfriend. “Can I have some time to think about it?” He pants against Jimmy's sinful lips.  

“The last thing I want is for you to feel pressured or obligated to say yes,” Jimmy says.

“Take all the time you need,” Cas murmurs, closer now, but still keeping his hands to himself.

“Thanks.” Dean's stomach growls and he can't help but glance at the table. “Can I eat now?”

Jimmy laughs and Cas rolls his eyes. “Go for it,” Cas says.

 

* * *

 

 

Dean’s on the fence about whether or not he should agree to the group sex all day. It isn’t until after his and Benny’s shifts are over that he realizes it could be fun.

They’re outside, leaning against a wall and enjoying the breeze.

“Hey, Benny?”

“Yes, brother?”

He’s so anxious he can’t even tease his friend for calling him brother. “I’ve got something to ask you… and I totally understand if you wanna say no -”

“Spit it out, Dean,” Benny says, a big grin on his face.

“Uh. So. Jimmy brought up a thing he wanted to try…” Dean’s voice trails off and he’s worried he’s gonna lose his nerve.

“Yes?” Benny asks. There's a smile in his voice, betraying his amusement.

“How would you feel about some casual sex with me and my boyfriends?” He blurts. If he doesn’t get it out now he never will.

Benny’s brows shoot up. “Boy, that’s a loaded question.”

“You don’t gotta answer now -”

“Think I could handle it depending on who I’d be fucking.”

“Uh.” Dean rubs at the back of his neck. “Pretty sure you’d be fucking me. Makes the most sense, doesn’t it?”

“I do like the sound of that. Anyone else invited to this little get together?”

Dean licks his lips nervously. This is the part he isn’t sure Benny will be keen on. Hell, Dean isn’t sure _he_ is completely okay with it just yet.

“Maybe. I don’t know if he’ll come… but Jimmy wants Sam to fuck him.”

“Huh. He’s a good choice.”

“How do you figure?” Dean gapes at him. It’s unreal how calm Benny is. “Sam doesn’t know Jimmy and Cas fuck. I don’t wanna lose Sam as my brother if he can’t handle it -”

“While I understand your concern this is _Sam_ we’re talkin’ about,” Benny says as if Dean needs reminding. “I’ve met him. He doesn’t strike me as the sort to drop his own brother for disagreein’ with matters of the heart.”

“Everybody has their limit, Benny. Maybe this is Sam’s.”

Benny watches Dean closely, eyes warm and thoughtful. “We’re all gonna be okay, brother. I know it doesn’t seem like it to you, but I’ve got a good feelin’ about this. Anyway… keep me updated?”

“Of course.”

The silence that follows has Dean itching to make a break for it - so he does.

 

* * *

 

 

The chat with Sam is harder for reasons no one can really fault him for. Thank fuck he has Cas and Jimmy to lean on.

“Why does this feel like an intervention?”

Okay, _that_ is a weird thing for his baby brother to say. “Not like that, man.”

“What’s going on then?”

Dean coughs and looks down at his hands. Fuck, this idea is the worst. Why the hell did he agree to this again?

“Are you attracted to me, Sam?” Jimmy asks, the words falling from his mouth quick and without a hint of shame. Dean wishes he could be as sure about this as Jimmy seems to be.

“What?” Sam squeaks.

“Do you wanna fuck me?”

Sam’s face flushes scarlet. “Are you serious?”

“We are,” Cas assures him because Dean can’t find his voice. “It’s okay, Sam. You can tell us. You’re not in trouble.”

“I’ve thought about it,” Sam says, sounding mortified. “I’m sorry.”

“We said you aren’t in trouble and we meant it,” Dean reminds him.

“Why? What does any of this matter?”

Jimmy and Cas exchange a significant look. “I want you too,” Jimmy says simply.

Sam gapes at him, saying nothing.

Dean reaches out a hand and rests it on Sam’s shoulder awkwardly. “It wouldn’t be just you and Jimmy, though…”

Sam’s breath hitches and he shakes his head. “I can’t believe this is happening.”

“Do you wanna participate in some casual group sex with us?”

“Dean, I swear to God if you’re fucking with me -”

“I wouldn’t do that, Sammy,” Dean promises. “What I’m asking is big. I realize that.”

Sam rubs a hand over his face. “This is so fucked up. You realize that, right?”

“S’not like me and you would be doing anything,” Dean says weakly.

“No?” Sam asks, head jerking up so he can stare right into Dean's soul.

“Of course not!” He can’t quite read his brother. To say it's terrifying and makes him freeze like a cornered rabbit would be an understatement.

“Wasn’t sure considering you guys are already doing the incest thing.”

Dean’s mouth falls open and he's forever grateful he decided against alcohol or food during this conversation otherwise he would have spat it out. “What are you -”

“Save it,” Sam says, holding up a hand. He looks at Jimmy closely. “I’m right, aren’t I? You and Cas fuck?”

Cas and Jimmy share a significant look before they both nod. “We do.”

“And Dean...”

“He’s known since the very beginning,” Jimmy says with a pleased smirk. “We’ve had no issues.”

“On the contrary. He gets off on watching or joining us,” Cas adds and Dean kind of wants to die even though he supposes it's important that Sam knows this part too. He'll find out eventually and it might not end well if they save this tidbit of information until they're all seeing each other naked for the first time.

Sam takes a deep breath and Dean’s preparing for the worst. Sam’s gonna call him a sick fuck, he’s gonna leave for good, they won’t be brothers anymore -

“I’ll do it.”

“Christ, don’t sound so excited, Sammy.”

“You guys are so happy,” Sam says, ignoring his comment. “As long as it’s safe and consensual I’ve got nothing against what you guys do behind closed doors. Kinda sucks you didn’t tell me earlier Dean, but I get it. It’s your story to share.”

“Yeah.” Dean shakes his head. “Holy shit, I can’t believe you said yes.”

“What now?”

“Depends. You wanna fuck around right away or save it for a rainy day?”

Sam snorts. “Nice, Dean… uh. Some time to process what you've told me would be nice -”

“What's there to process?” Jimmy purrs, slapping a hand down on Sam’s thigh, making him gasp. “You’re gonna see your brother naked, no big deal. It’s not like you’ll have time to focus on it. You’ll be too busy fucking me stupid.”

Sam swallows thickly and stands up, banging his shins against the coffee table and letting out a hiss of pain. “I’ll be right back,” he says and stumbles off to the bathroom.

Dean pouts. “If you scared my brother away I’m sleeping on the couch.”

Cas rolls his eyes. “No, you won’t.”

“Don’t pretend you have any clue _what_ I’ll do, Cas -”

“You won’t do it because neither of us wants you bitching about your back in the morning,” Jimmy interrupts.

Dean grumbles and crosses his arms.

“Dean,” Cas says, his tone making him hot all over.

“Fuck you for being so hot,” he says, sighing in annoyance. “Fine. Sorry for threatening to sleep without you, Jimmy.”

“I’m sorry for making your brother hide in the bathroom.”

 

* * *

 

 

Dean can see everything. He can see Sam’s thick fingers slowly disappearing inside of Jimmy, coaxing him open. He can see Sam’s tongue darting out between his teeth. He can see that big, wet cock arching toward his belly - he can see it _all._

“Come on,” Dean whines even though he _knows_ Cas and Benny are purposely holding back. The plug filling him up is bigger than anything he’s ever taken up his ass and he can barely breathe due to the intensity of it. His hole is so loose Cas and Benny will have no issue slipping inside him. Which, he supposes, is the point of the plug to begin with.

“Not yet,” Cas says, using the remote control to turn the butt plug on and make it vibrate.

“Son of a bitch,” Dean gasps and starts to wiggle on the floor. No way can he stay still without being restrained.

“Too much?” Cas asks, thumb hovering over the off button, ready to offer temporary relief.

“N-no,” Dean grits out. “I can take it.”

He just wishes he had two cocks in his ass so he wasn’t busy staring at _Sam’s_ dick _._ He wishes he wasn’t facing them because he sees the exact moment Sam enters Jimmy. Jimmy’s on all fours, the side of his face pressed against the floor, lazily rolling his hips as he gazes at Dean. There’s a wicked glint in his eyes and even though Jimmy _said_ he didn’t expect Dean to play with Sam it’s like he’s silently asking him if he wants to.

Dean leans in when he can’t take the looks any longer and kisses Jimmy with an almost vicious intensity. It soothes the uncertainty inside him and he’s fucking grateful he’s able to go more than two seconds without looking at Sammy.

Benny, who has kept his hands mostly to himself, spanks Dean’s plug unexpectedly, making him moan into Jimmy’s mouth. “Not you too,” Dean says. “All of you are a bunch of sadists.”

“Only when it comes to you, brother.”

“That’s worse,” Dean complains.

Sam slows his thrusts, eyes settling on Dean. “You’re making it really fucking hard to concentrate,” he growls. “Anyone have a gag that I can shut him up with?”

Why is he not disgusted by that idea? He’d like to blame the vibrating plug in his ass…

“That would require one of us to go get it,” Benny points out, running his fingers through Dean’s hair gently. “And I doubt many of us feel much of a desire to do that.”

Cas leans down to suck hickeys into Dean’s thighs, humming in agreement. “Maybe for round two. I have a ring gag that would look lovely on him. Then we could force his mouth to stay open and use it however we want without hearing him complain.”

“Seriously? You actually have one?” Sam's eyes are wide and it's kind of adorable. 

“Yes, Sam,” Cas says while tonguing Dean’s prince Albert. “I have many toys that I plan on using on your brother eventually.”

“Can I…” Sam swallows hard then shakes his head. “Nevermind.”

“No.” Cas surges up and grabs Sam’s chin. “Don’t do that. What do you want?"

“C-Can I put it on him?” Sam groans and Dean almost comes right there.

_Fuck yes._

Maybe he said it out loud because Sam’s staring at him. “Say it.”

“You can put the gag on me, Sammy.”

“Especially if you plan on trying out his mouth afterward, “Jimmy says, fucking himself on Sam’s cock.

Sam lets out a hiss, eyes darkening and slams his hips into Jimmy _hard._ “I dunno if that’s a good idea.”

_Why do you look so into it then?_

“But fucking your brother is fun,” Jimmy gasps, eagerly meeting Sam’s thrusts.

“It’s true,” Cas says seriously, pinching Dean’s nipples.

“P-Please,” Dean whimpers. “Guys, I really need you to fuck me.”

“What do you think?” Benny asks, glancing at Cas. “Has he waited long enough?”

Cas answers by turning the vibrating plug off and carefully pulling it out. Dean fucking _sobs_ because he feels so damn _empty._ His insides have fallen out. He’s hollow.

“Climb onto Benny’s cock,” Cas breathes in his ear. “And it won’t hurt my feelings if you fantasize that I’m someone else.”

Dean wishes he could tell Cas how fucked up that is but his dick is leaking far too much for it not to mean _something._ So all he can do is nod dumbly and straddle Benny, pleasantly surprised that Cas takes control and lowers him onto Benny’s cock himself. Then he slips a couple fingers inside of Dean to make sure he’s open enough to take Cas too before filling him up.

 

* * *

 

 

“Something’s up with you,” Jimmy blurts out. “What is it?”

“You can tell us,” Cas adds.

They’re all showering together, Cas behind him and Jimmy in front of him - so Dean’s trapped.

“It’s nothing,” Dean says stubbornly, shaking his head. “I’m fine.”

“You are _not_ fine,” Cas growls. “You’ve been withdrawn for days.”

Dean slumps his shoulders in defeat. His gut tells him they aren’t going to let this go. He’s afraid to say it - terrified, really. But the knowledge is slowly eating him up from the inside out.

“I don’t want Sammy to be a one-time thing.”

“Okay,” Jimmy says, blindsiding him. “We’ll see what Sam’s comfortable with. For all we know he’s feeling the exact same way.”

“I’m not opposed to that idea,” Cas murmurs, cleaning soap off of Dean’s back.

“You realize I’m talking about wanting something permanent, right? I… I don’t want it to be a casual fuck.”

“Yes, Dean. And we’re okay with it. Besides, how hypocritical would we be if we got upset over you wanting to be closer to your brother when _we_ pushed you together?"

“Fair point,” Dean says, letting out a shaky breath.

Cas runs the washcloth over his hole and Dean whines in frustration.

“Don’t worry,” Cas whispers into his skin. “After we get out of the shower we’ll call Sam and invite him over.”

“We’ve got you,” Jimmy says before kissing Dean and Cas breathless. “We’ve all got each other and we’re gonna work it out.”

Maybe Dean’s delusional, maybe adding a fourth person into their relationship is doomed to fail, but he’s feeling lighter and more hopeful already.

**Author's Note:**

> Thanks for reading! Kudos and comments give me life, so please consider taking an extra moment out of your day and let me know if you liked this fic. :)
> 
> I'm samanddeaninpanties on Tumblr if you wanna stop by and chat!

**Works inspired by this one:**

  * [Art for Why Does it Have to Be (Wrong or Right)](https://archiveofourown.org/works/10930746) by [Mayalaen](https://archiveofourown.org/users/Mayalaen/pseuds/Mayalaen)




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